192431-33-7

Basic information

• Product Name: (3aR,7aS)-N-[(S)-α-Methylbenzyl]-3a-(2-nitrophenyl)octahydroindol-4-one
• Synonyms: (3aR,7aS)-N-[(S)-α-Methylbenzyl]-3a-(2-nitrophenyl)octahydroindol-4-one
• CAS NO: 192431-33-7
• Molecular Weight: 364.444
• Mol File: 192431-33-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3aR,7aS)-N-[(S)-α-Methylbenzyl]-3a-(2-nitrophenyl)octahydroindol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,7aS)-N-[(S)-α-Methylbenzyl]-3a-(2-nitrophenyl)octahydroindol-4-one(192431-33-7)
• EPA Substance Registry System: (3aR,7aS)-N-[(S)-α-Methylbenzyl]-3a-(2-nitrophenyl)octahydroindol-4-one(192431-33-7)

Safety Data

• Hazardous Substances Data: 192431-33-7(Hazardous Substances Data)

Upstream product

• 138040-06-9 3-allyloxy-2-(o-nitrophenyl)-2-cyclohexenone 
• 504-02-9 1,3-cylohexanedione 
• 609-73-4 o-nitroiodobenzene 
• 138040-07-0 2-Allyl-2-(2-nitrophenyl)-1,3-cyclohexanedione 
• 17279-30-0 (S)-(-)-α-methylbenzylamine hydrochloride 
• 176042-32-3 2-(formylmethyl)-2-(o-nitrophenyl)-1,2-cyclohexanedione 

Downstream Products

• 6883-33-6 (-)-tubifolidine 
• 222162-04-1 (3aR,7aS)-3a-(2-Nitro-phenyl)-4-oxo-5-phenylselanyl-octahydro-indole-1-carboxylic acid 1-chloro-ethyl ester 
• 192431-40-6 (3aR,7aS)-3a-(2-Nitro-phenyl)-1-(4-trimethylsilanyl-but-2-ynyl)-1,2,3,3a,7,7a-hexahydro-indol-4-one 
• 192574-05-3 (-)-7-(2-nitrophenyl)-2-vinylidene-4-azatricyclo[5.2.2.0^4,8]undecan-11-one 
• 222162-01-8 (3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one 
• 222162-02-9 (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one 
• 222162-00-7 (3aR,7aS)-3a-(2-Nitro-phenyl)-4-oxo-2,3,3a,4,7,7a-hexahydro-indole-1-carboxylic acid 1-chloro-ethyl ester 
• 57-24-9 strychnidin-10-one 
• 466-85-3 (17R,19E)-17,18-epoxy-cur-19-en-17-ol 
• 192431-42-8 (3aR,7aS)-3a-(2-Nitro-phenyl)-4-oxo-octahydro-indole-1-carboxylic acid 1-chloro-ethyl ester 

Relevant articles and documents

Enantioselective Total Synthesis of Wieland-Gumlich Aldehyde and (-)-Strychnine

A total synthesis of (-)-strychnine in 15 steps from 1,3-cyclohexanedione in 0.15% overall yield is described. The sequence followed in the assembling of rings is: E → AE [2-(2-nitrophenyl)-1,3-cyclohexanedione] → ACE (3a-aryloctahydroindol-4-one) → ACDE (arylazatricyclic core) → ABCDE (strychnan skeleton) → ABCDEF (Wieland-Gumlich aldehyde) → ABCDEFG (strychnine). The key steps of the synthesis are the enantioselective construction of the 3a-(2-nitrophenyl)-octahydroindol-4-one ring system and the closure of the piperidine ring by a reductive Heck cyclization to generate the pivotal intermediate (-)-14. In contrast, a Lewis acid promoted α-alkoxy-propargylic silane-enone cyclization did not lead to synthetically useful azatricyclic ACDE intermediates. The introduction of C-17 and the closure of the indoline ring by reductive amination of the α-(2-nitrophenyl) ketone moiety complete the strychnan skeleton from which, via the Wieland-Gumlich aldehyde, the synthesis of (-)-strychnine is achieved.

A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (±)- and (-)-tubifolidine, (±)-akuammicine, (±)-19,20-dihydroakuammicine, (±)-norfluorocurarine, (±)-ec

A general strategy for the synthesis of pentacyclic Strychnos alkaloids with the curan skeleton has been developed. It utilizes 3a-(2-nitrophenyl)hexahydroindol-4-one (23), which was prepared from 2-allyl-2-(2-nitrophenyl)-1,3-cyclohexanedione (15), as th